Is parking easy in Oregon, WI?

As of early 2026, 94% of users say parking is easy

Is Oregon, WI dog-friendly?

As of early 2026, 94% of users say it's dog friendly

Does Oregon, WI have sidewalks?

As of early 2026, 92% of users say there are sidewalks

Do kids play outside in Oregon, WI?

As of early 2026, 87% of users say kids play outside

Would people walk alone at night in Oregon, WI?

As of early 2026, 86% of users say people would walk alone at night

Are yards well-kept in Oregon, WI?

As of early 2026, 85% of users say yards are well-kept

Is a car needed in Oregon, WI?

As of early 2026, 84% of users say car is needed

Are the streets well-lit in Oregon, WI?

As of early 2026, 80% of users say streets are well-lit

Does Oregon, WI show holiday spirit?

As of early 2026, 80% of users say there's holiday spirit

As of early 2026, 77% of users say it's quiet

Is Oregon, WI walkable to restaurants?

As of early 2026, 68% of users say it's walkable to restaurants

Do residents of Oregon, WI plan to stay at least 5 years?

As of early 2026, 68% of users say they plan to stay for at least 5 years

Are neighbors friendly in Oregon, WI?

As of early 2026, 68% of users say neighbors are friendly

Is there wildlife in Oregon, WI?

As of early 2026, 58% of users say there's wildlife

Is Oregon, WI walkable to grocery stores?

As of early 2026, 48% of users say it's walkable to grocery stores

Are there community events in Oregon, WI?

As of early 2026, 43% of users say there are community events

OFF MARKET

4458 Hill Rd
Oregon, WI 53575

3 Beds
3 Baths
2,910 sqft (on 7.10 acres)

$935,000

Trulia Estimate

as of Aug 6, 2026

Est. Refi. Payment $6,000/mo*

Refinance Your Home

$935,000

Trulia Estimate

as of Aug 6, 2026

Est. Refi. Payment $6,000/mo*

Refinance Your Home

3 Beds

3 Baths

2,910 sqft

(on 7.10 acres)

Local Information

Map ViewExplore the area around 4458 Hill Rd.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1992

Lot Size

7.1 acres

Living Area

2,910 sqft

Price/Sqft

$321

Parking

Garage

About this House

Secluded, wooded, beautifully updated and expanded Ranch home w/ Oregon Schools! Additional 1212 sq ft added, vaulted ceilings in great room, 2 gas fireplaces, high quality 3 season porch, gourmet kitchen w/ granite counter tops, cherry cabinetry, red birch hardwood flooring throughout, TONS of windows overlooking close to 2,000 trees planted in past ten years w/ hiking trails & private, stocked 10 ft deep fishing pond on 7 acres. 60x40 outbuilding w/ bath, heated & insulated workshop. A-2 zoning, tons of possibilities.
For 24 hour information, please call 800-837-1483 code #2365

4458 Hill Rd, Oregon, WI 53575 is a 3 bedroom, 3 bathroom, 2,910 sqft single-family home built in 1992. It last sold for $540,000 on Dec 1, 2016. It is currently off market. The Trulia Estimate is $935,000, with a rent estimate of $3,334/month.

Home Details for 4458 Hill Rd

Interior Features
Heating & Cooling Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 1Floors: Tile, Hardwood
Interior Details Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher

Property Information
Year Built Year Built: 1992
Property Type / Style Property Type: Single Family Home

Exterior Features
Exterior Home Features Exterior: Vinyl
Parking & Garage GarageParking: Garage Attached, Garage Detached

Community
Units in Building: 1

Lot Information
Lot Area: 7.10 acres

Price History for 4458 Hill Rd

Date	Price	Event	Source
12/01/2016	$540,000	Sold	SCWMLS #1785015
Recording Date 12/01/2016 County Transfer Tax N/A Total Transfer Tax N/A
09/15/2016	$559,900	Pending	Agent Provided

09/06/2016	$559,900	Listed For Sale	Agent Provided

Market trends in Oregon

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

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Property Tax and Assessment

Year	2024
Tax	$8,962
Assessment	$686,400

Home facts updated by county records

Comparable Sales for 4458 Hill Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
4285 Rutland Dunn Town Line Rd, Oregon, WI	1.26	Single-Family Home	$773,300	04/27/26	3	3	2,617
1089 US Highway 14, Oregon, WI	0.98	Single-Family Home	$1,100,000	10/23/25	4	3.5	4,352
491 Concord Dr, Oregon, WI	1.06	Single-Family Home	$730,000	06/10/26	4	3	4,284
938 Johnson Ave, Oregon, WI	1.36	Single-Family Home	$530,000	03/26/26	3	2.5	1,932
4696 Rutland Dunn Town Line Rd, Oregon, WI	1.54	Single-Family Home	$900,000	03/16/26	4	3	3,694
1349 Sunrise Rd, Oregon, WI	0.94	Single-Family Home	$1,800,000	10/10/25	4	4.5	5,803
901 County Road Mm, Oregon, WI	1.81	Single-Family Home	$832,000	04/22/26	3	3	3,068
581 Concord Dr, Oregon, WI	1.11	Single-Family Home	$850,000	12/17/25	5	3.5	4,059
994 Autumn Blaze Way, Oregon, WI	1.40	Single-Family Home	$617,000	10/17/25	4	3	2,722
445 Foxfield Ct, Oregon, WI	1.37	Single-Family Home	$759,900	06/15/26	4	2.5	3,006

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $2,007,900
5 bd
4 ba
5,764 sqft
4488 Hill Rd,
Oregon, WI 53575
OFF MARKET
1185 Highway 14,
Oregon, WI 53575
FOR SALE
OPEN SAT, 11-12PM
$379,900
3 bd
2.5 ba
1,824 sqft
530 Lexington Dr,
Oregon, WI 53575
OFF MARKET
Est. $359,900
3 bd
2 ba
1,832 sqft
524 Lexington Dr,
Oregon, WI 53575
SOLD
MAR 10, 2026
$365,000
3 bd
1.5 ba
1,574 sqft
550 Lexington Dr,
Oregon, WI 53575
SOLD
MAR 30, 2026
$375,000
3 bd
2.5 ba
1,842 sqft
558 Lexington Dr,
Oregon, WI 53575
SOLD
OCT 23, 2025
$1,100,000
4 bd
3.5 ba
4,352 sqft
1089 US Highway 14,
Oregon, WI 53575
SOLD
OCT 10, 2025
$1,800,000
4 bd
4.5 ba
5,803 sqft
1349 Sunrise Rd,
Oregon, WI 53575
SOLD
JAN 16, 2026
$370,000
3 bd
2.5 ba
1,787 sqft
562 Lexington Dr,
Oregon, WI 53575
SOLD
JUL 17, 2026
$339,000
3 bd
2 ba
2,130 sqft
450 Concord Dr,
Oregon, WI 53575
SOLD
JUL 23, 2026
$365,000
3 bd
2.5 ba
1,698 sqft
452 Concord Dr,
Oregon, WI 53575
OFF MARKET
Est. $350,100
3 bd
2.5 ba
1,698 sqft
452 Concord Dr #452,
Oregon, WI 53575

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Additional Cost

Assigned Schools

These are the assigned schools for 4458 Hill Rd.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Oregon

At least 64 Trulia users voted on each feature.

94 % Say parking is easy
94 % Say it's dog friendly
92 % Say there are sidewalks
87 % Say kids play outside
86 % Say people would walk alone at night
85 % Say yards are well-kept
84 % Say car is needed
80 % Say streets are well-lit
80 % Say there's holiday spirit
77 % Say it's quiet
68 % Say it's walkable to restaurants
68 % Say they plan to stay for at least 5 years
68 % Say neighbors are friendly
58 % Say there's wildlife
48 % Say it's walkable to grocery stores
43 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Tanya Hoppe
Resident
2y ago
"Friendly and family orientated little Town with great school district. Our neighbors are great and watch out for each other. "
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Khockett58
Resident
5y ago
"Village Oregon Great place to live. Great schools & sport Great food places to eat. Doctor clinics Gad stations Banks. Small town but close to drive in to Madison or Stoughton And other cities "
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Lysagrant
Resident
5y ago
"15 minute drive from Madison. No public transportation. Easy access to rate 14. Not much traffic even at rush hour."
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Tjrbackstroker
Visitor
6y ago
"A quick drive up to Madison. The area is very drivable with not too much traffic. It is very easy to get on the highway."
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Kelly J. P.
Resident
6y ago
"Love it here! Best move to call this home for our family to grow. Super nice community. We love our neighbors and enjoy to small town feel that Oregon has to offer & also super close to Madison for fun nights out!"
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Ken D.
Resident
7y ago
"Great schools, convenient to madison, stoughton and Fitchburg. Housing market is booming, low crime"
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Rachel
Resident
7y ago
"To always keep an eye on your kids no matter how safe a neighborhood is deemed to be. Oregon is a great place to live!"
1
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miltydog
12y ago
"Wonderful schools and a strong sense of community"
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Donna R. B.
12y ago
"Very private rural subdivision....may be a longer drive to madison but for the beautiful lot and privacy a huge bonus"
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Stevie K.
12y ago
"If you like your privacy, multi level living, looking out the back you feel as if you are in the woods! Lots of updates and well cared for. Great neighbors, I used to be one but moved out West, so I have personally been inside and it's great! It is located on a private circle with little traffic! It's definitely a must see!"
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Stefan
14y ago
"This area of Oregon is excellent. The schools are the best. The neighborhoods around Lincoln Road, County A and Hillcrest are nice, but, drivers have no regard for safety at all. Stay off these roads if you bike or run. Farm families are very nice, too. You will love bringing up children in this area. Oregon is the best community in the Madison area for kids and your families to live."
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